Chemical and enzymatic diastereoselective cleavage of β-d-galactopyranosylsulfoxides

✍ Scribed by Noureddine Khiar; Inés Alonso; Natividad Rodriguez; Alfonso Fernandez-Mayoralas; Jesus Jimenez-Barbero; Ofelia Nieto; Felix Cano; Concepción Foces-Foces; Manuel Martin-Lomas

• Book ID: 104258248
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 210 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10164-2

✦ Synopsis

The self induced diastereoselective oxidation of several thio-~-D-galactopyranosides to the corresponding sulfoxides, has been shown to occur in high yield. Up to 74% diastereomeric excess could be obtained depending on the structure and the conformation of the starting thioglycoside.Rs and Ss Phenylsulfinyl-13-D-galactopyranosides have been obtained in optically pure forms, their chemical as well as enzymatic hydrolysis with triflic acid and with 13-galactosidase have been shown to proceed diastereoselectively, the structure of the sulfoxide 4'S with the S configuration at the sulfinyl sulfur has been determined by X-ray analysis.